Ammonium Chloride → HCID 90375013, compound

HRID 1507161Notes

Reaction equation

HRID 1507161 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[CH:26]=[C:25]([C:27](OCC)=[O:28])[CH:24]=[CH:23][N:22]=1)[CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][N:17]([CH3:19])[CH3:18])[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CCO>[CH3:18][N:17]([CH2:16][CH:13]1[CH2:12][CH2:11][CH:10]([CH2:9][N:8]([CH2:20][C:21]2[CH:26]=[C:25]([CH2:27][OH:28])[CH:24]=[CH:23][N:22]=2)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:15][CH2:14]1)[CH3:19]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 117738641HCID 117738641, compound

Product 1

HCID 90375013HCID 90375013, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

By General Procedure U from ethyl 2-({[(tert-butoxy)carbonyl]({4-[(dimethylamino)methyl]cyclohexyl}methyl)amino}methyl)pyridine-4-carboxylate) (1.0 equiv.) in EtOH. Stirred at reflux for 2 hours. Cooled to room temperature and sat. NH4Cl solution was added. Evaporated to dryness. Purification by column chromatography (DCM, MeOH (10%) and HN4OH (1%)) gave the title product as light yellow oil. 1H NMR (300 MHz, chloroform-d): δ ppm 8.41 (d, 1H), 7.17 (m, 2H), 4.65 (s, 2H), 4.50 (d, 2H), 3.10 (m, 2H), 2.17 (s, 6H), 2.07 (d, 2H), 1.74 (m, 4H), 1.41 (m, 11H), 0.87 (m, 4H).

Workup

  1. temperatureat reflux for 2 hours
  2. customEvaporated to dryness
  3. customPurification by column chromatography (DCM, MeOH (10%) and HN4OH (1%))

Sources & evidence

ORD record
ord-5dfe2e0bc171426e81bce66e4dce3b58
Source dataset
uspto-grants-2015_12
Patent number
US09221801B2

Reaction notes

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